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DrugBank Gentian Violet (APRD00998)

Show Similar Structure(s) for Approved Drugs

Creation Date 2005/12/21 02:59:09 GMT

Last Update Feb 01, 2007

Accession Number APRD00998

Generic Name Gentian Violet

1. Adergon 2. Aizen Crystal Violet 3. Aizen Crystal Violet Extra Pure 4. Aniline Violet 5. Aniline Violet pyoktanine 6. Atmonil 7. Avermin 8. Axuris 9. Badil 10. Basic Violet 3 11. Basic Violet BN 12. Basic Violet-3 13. Bismuth Violet 14. Brilliant Violet 5B 15. C.I. Basic Violet 3 16. Calcozine Violet 6BN 17. Calcozine Violet C 18. Crystal Violet 19. Crystal Violet 10B 20. Crystal Violet 5BO 21. Crystal Violet 6B Brand 22. Crystal Violet 6BO Names/Synonyms 23. Crystal Violet AO 24. Crystal Violet AON 25. Crystal Violet BP 26. Crystal Violet BPC 27. Crystal Violet Extra Pure 28. Crystal Violet Extra Pure APN 29. Crystal Violet Extra Pure APNX 30. Crystal Violet FN 31. Crystal Violet HL2 32. Crystal Violet O 33. Crystal Violet Pure DSC 34. Crystal Violet Pure DSC Brilliant 35. Crystal Violet SS 36. Crystal Violet Technical 37. Crystal Violet USP 38. Crystal Violet base 39. Crystal Violet chloride 40. Crystal Violet chloride salt 41. GV-Eleven 42. Genapax 43. Gentersal 44. Gentiaverm 45. Genticid 46. Gentioletten 47. Gvs 48. Hecto Violet R 49. Hectograph Violet SR 50. Hexamethyl Violet 51. Hexamethylpararosaniline chloride 52. Hidaco Brilliant Crystal Violet 53. Hidaco crystal Violet 54. Meroxyl-Wander 55. Meroxylan-Wander 56. Methyl Violet 10B 57. Methyl Violet 10BD 58. Methyl Violet 10BK 59. Methyl Violet 10BN 60. Methyl Violet 10BNS 61. Methyl Violet 10BO 62. Methyl Violet 5BNO 63. Methyl Violet 5BO 64. Methyl Violet 6B 65. Methyl violet 66. Methylrosaniline chloride 67. Mitsui Crystal Violet 68. Oxiuran 69. Oxycolor 70. Oxyozyl 71. Paper Blue R 72. Plastoresin Violet 5BO 73. Pyoktanin 74. Vermicid 75. Vianin 76. Viocid 77. Violet 5BO 78. Violet 6BN 79. Violet CP 80. Violet XXIII 81. crystal violet for microscopy 82. gentian violet gr 83. gention violet alchoholic staining solution 84. methylrosanilinium chloride

1. Blu Kote Dr Naylors (Acriflavine + Gentian Violet + Glycerine + Isopropyl Alcohol + Sodium Propionate + Urea) 2. Blue Lotion (Gentian Violet + Methylene Blue + Tannic Acid) 3. Co-Op Pinkeye Spray (Gentian Violet + Neomycin (Neomycin Sulfate)) 4. Cristisol (Acriflavine + Gentian Violet + Isopropyl Alcohol) 5. Pink Eye Guard (Allantoin + Boric Acid + Gentian Violet) Brand Name Mixtures 6. Pink Eye Spray (Furfural + Gentian Violet + Isopropyl Alcohol + Methylene Blue + Phenylmercuric Nitrate (Basic) + Tetrahydrofurfuryl Alcohol + Urea) 7. Pinkeye Spray (Gentian Violet + Neomycin (Neomycin Sulfate)) 8. Triple Dye (Brilliant Green + Gentian Violet + Proflavine Hemisulfate) 9. Wound & Pinkeye Spray (Gentian Violet + Neomycin (Neomycin Sulfate)) 10. Wound Kote Gentian Violet Spray Wound Dre (Acriflavine + Furfural + Methyl Violet + Sodium Propionate + Urea)

Chemical IUPAC Name [4-[bis(4-dimethylaminophenyl)methylidene]-1-cyclohexa-2,5-dienylidene]-dimethyl-azanium

Chemical Formula C25 H30 N3+ Chemical Structure

CAS Registry Number 14426-25-6

InChI=1/C25H30N3/c1-26(2)22-13-7-19(8-14-22)25(20-9-15-23(16-10-2 InChi Identifier 0)27(3)4)21-11-17-24(18-12-21)28(5)6/h7-18H,1-6H3/q+1

KEGG Compound ID D01046

Substance: 538591 PubChem ID Compound: 3468

ChEBI ID Not Available

PharmGKB ID PA449755

HET ID Not Available

SwissProt ID Not Available

GenBank ID Not Available

Drug ID Number [DIN] 00050857

RxList Link Not Available

FDA Label Not Available Material Safety Data Click Here for MSDS File (html) Sheet (MSDS) Synthesis Reference Not Available

Molecular Weight 372.526 g/mol

Melting Point 215 °C

H2O Solubility 4 mg/mL

State Solid

LogP/Hydrophobicity 3.18 pKa/Isoelectric Point Not Available

NMR Spectrum Not Available

Mass Spectrum Not Available

MOL File Image View 2D Structure

MOL File Text Click Here for MOL File

SDF File Click Here for SDF File PDB File Calculated Not Available Image PDB File Calculated Not Available Text PDB Experimental ID Not Available

Smiles String CN(C)C1=CC=C(C=C1)C(=C2C=CC(=[N+](C)C)C=C2)C3=CC=C(C=C3)N(C)C

Drug Type Approved Drug Drug Category Anti-Infective Agents, Local

For the treatment of bacterial and fungal infections inside the mouth (thrush) and skin, also Indication for the prevention of transmission of Chagas' disease (as a blood additive).

Gentian violet is a mutagen, a mitotic poison, and a clastogen. Gentian violet has been used in medicine for almost 100 years: as an antiseptic for external use, as a topical antibiotic, as a topical antifungal agent, as an antihelminthic agent by oral administration, and more Pharmacology recently, as a blood additive to prevent transmission of Chagas' disease. It is thought to work by binding to the DNA of target organisms and causing disruption, mutation or inhibition of DNA replication.

In aqueous solutions Gentian violet (GV) dissociates into positive (GV+)and negative ions (Cl-) that penetrate through the wall and membrane of both gram-positive and gram-negative bacterial cells. The GV+ interacts with negatively charged components of bacterial cells including the lipopolysaccharide (on the cell wall), the peptidoglycan and DNA. A similar cell penetration and DNA binding process is thought to take place for fungal cells as well. Because Gentian violet is a mutagen and mitotic poison, cell growth is consequently Mechanism of Action inhibited. A photodynamic action of gentian violet, apparently mediated by a free-radical mechanism, has recently been described in bacteria and in the protozoan T. cruzi. Evidence also suggests that gentian violet dissipates the bacterial (and mitochondrial) membrane potential by inducing permeability. This is followed by respiratory inhibition. This anti-mitochondrial activity might explain gentian violet's efficacy towards both bacteria and yeast with relatively mild effects on mammalian cells.

Absorption Not Available

LD =420 mg/kg (rat, oral). Oral administration can cause gastrointestinal irritation, and Toxicity 50 intravenous injection can cause depression in the white blood cell count.

Protein Binding Not Available

Biotransformation Primarily hepatic, mostly demethylation

Half Life Not Available

Liquid Dosage Forms Tincture

Patient Information Not Available

Interactions Not Available

Contraindications Not Available

Drug Reference http://www.pharmgkb.org/views/index.jsp?objId=PA449755&objCls=Drug

Organisms Affected Yeast and other fungi, bacteria and protozoans Phase 1 Metabolizing Not Available Enzyme Phase 1 Metabolizing Not Available Enzyme Sequence Phase 1 Metabolizing Not Available Enzyme SwissProt ID Drug Target 1 Drug Target 1 Name DNA Drug Target 1 Gene Not Applicable Name Drug Target 1 Deoxyribonucleic acid Synonyms Drug Target 1 Protein > Dickerson dodecamer Sequence CGCGAATTCGCG(example) Drug Target 1 Number 12 of Residues Drug Target 1 7656 (double stranded) g/mol Molecular Weight Drug Target 1 Not Available Theoretical pI Function: information storage Function: information transfer || Biological process: DNA replication and chromosomal cycle Biological process: DNA replication Biological process: DNA-dependent DNA replication Drug Target 1 GO Biological process: DNA replication, synthesis of RNA primer Classification Biological process: transcription Biological process: transcription, DNA dependent || Cellular component: cell Cellular component: intracellular Cellular component: nucleus Cellular component: mitochondria Drug Target 1 General Biological information storage and information transfer Function DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double Drug Target 1 Specific helix and held together by hydrogen bonds. The sequence of nucleotides determines Function hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

Map03030 DNA replication Drug Target 1 Pathway Map03020 RNA transcription

DNA + DNA polymerase + nNTP = 2 DNA + nNDP ; DNA + RNA polymerase + NTP = Drug Target 1 Reaction mRNA + nNDP Drug Target 1 Pfam None Domain Function Drug Target 1 Signals None Drug Target 1 Transmembrane None Regions Drug Target 1 Essential Essentiality Drug Target 1 GenBank Not Applicable ID Protein Drug Target 1 Not Applicable SwissProt ID Drug Target 1 PDB ID 1BNA Drug Target 1 3D Click for PDB File Structure Text Drug Target 1 3D View 3D Structure Structure Image Drug Target 1 Cellular Nucleus and mitochondria Location Drug Target 1 Gene > DNA, Dickerson dodecamer Sequence CGCGAATTCGCG Drug Target 1 GenBank Not Applicable ID Gene Drug Target 1 All chromosomes Chromosome Location Drug Target 1 Locus All loci

Drug Target 1 SNPs Not Available Drug Target 1 15556400 References

Last Update: Nov 06, 2006